#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:03:47 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178418 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/39/4023938.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023938
loop_
_publ_author_name
'Amos B. Smith, III'
'László Kürti'
'Akin H. Davulcu'
'Young Shin Cho'
'Kazuyuki Ohmoto'
_publ_contact_author_address
;Amos B. Smith, III
Rhodes-Thompson Professor
Department of Chemistry
University of Pennsylvania
Philadelphia, PA 19104-6323
smithab@sas.upenn.edu
http://absmithgroup.chem.upenn.edu/absgroup 
;
_publ_contact_author_email       smithab@sas.upenn.edu
_publ_contact_author_fax         '215) 898-5129'
_publ_contact_author_name        'Amos B. Smith, III'
_publ_contact_author_phone       '(215) 898-4860'
_publ_section_title
;
 Indole Diterpene Synthetic Studies: Development of a Second-Generation
 Synthetic Strategy for (+)-Nodulisporic Acids A and B
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4611
_journal_page_last               4620
_journal_paper_doi               10.1021/jo062423a
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C17 H17 N O'
_chemical_formula_weight         251.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.239(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.006(3)
_cell_length_b                   9.2753(16)
_cell_length_c                   17.100(4)
_cell_measurement_temperature    143(1)
_cell_volume                     2602.4(9)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21039
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5987
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.348
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.348
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.1162
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3065
_refine_ls_wR_factor_ref         0.3240
_reflns_number_gt                3631
_reflns_number_total             4521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062423asi20061218_094252.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/n     '
_cod_database_code               4023938
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7423(2) 0.4334(4) 0.6963(2) 0.0591(10) Uani 1 1 d . . .
N1 N 0.47157(19) 0.3493(3) 0.57019(19) 0.0304(7) Uani 1 1 d . . .
C1 C 0.5461(2) 0.2837(4) 0.5937(2) 0.0293(9) Uani 1 1 d . . .
C2 C 0.5625(2) 0.1312(4) 0.5808(2) 0.0314(9) Uani 1 1 d . . .
H2a H 0.5682 0.1176 0.5263 0.042 Uiso 1 1 calc R . .
H2b H 0.5175 0.0721 0.5871 0.042 Uiso 1 1 calc R . .
C3 C 0.6410(3) 0.0861(5) 0.6427(3) 0.0416(10) Uani 1 1 d . . .
H3a H 0.6312 0.0803 0.6960 0.055 Uiso 1 1 calc R . .
H3b H 0.6571 -0.0089 0.6288 0.055 Uiso 1 1 calc R . .
C4 C 0.7092(3) 0.1917(5) 0.6450(3) 0.0435(10) Uani 1 1 d . . .
H4a H 0.7233 0.1869 0.5937 0.058 Uiso 1 1 calc R . .
H4b H 0.7567 0.1617 0.6871 0.058 Uiso 1 1 calc R . .
C5 C 0.6900(2) 0.3476(5) 0.6606(2) 0.0399(10) Uani 1 1 d . . .
C6 C 0.6045(2) 0.3883(4) 0.6305(2) 0.0323(9) Uani 1 1 d . . .
C7 C 0.5625(3) 0.5234(4) 0.6320(2) 0.0362(10) Uani 1 1 d . . .
C8 C 0.5735(3) 0.6668(4) 0.6605(2) 0.0458(11) Uani 1 1 d . . .
H8 H 0.6251 0.7020 0.6859 0.061 Uiso 1 1 calc R . .
C9 C 0.5051(4) 0.7534(4) 0.6493(3) 0.0496(12) Uani 1 1 d . . .
H9 H 0.5130 0.8480 0.6676 0.066 Uiso 1 1 calc R . .
C10 C 0.4234(3) 0.7095(4) 0.6119(3) 0.0491(12) Uani 1 1 d . . .
H10 H 0.3797 0.7725 0.6068 0.065 Uiso 1 1 calc R . .
C11 C 0.4120(3) 0.5687(4) 0.5836(3) 0.0402(10) Uani 1 1 d . . .
C12 C 0.4816(2) 0.4914(4) 0.5941(2) 0.0318(9) Uani 1 1 d . . .
C13 C 0.3423(3) 0.4672(4) 0.5433(3) 0.0430(10) Uani 1 1 d . . .
H13a H 0.3161 0.4989 0.4886 0.057 Uiso 1 1 calc R . .
H13b H 0.3019 0.4636 0.5741 0.057 Uiso 1 1 calc R . .
C14 C 0.3835(2) 0.3144(4) 0.5424(2) 0.0313(9) Uani 1 1 d . . .
H14 H 0.3705 0.2767 0.4869 0.042 Uiso 1 1 calc R . .
C15 C 0.3608(2) 0.2051(4) 0.5982(2) 0.0346(9) Uani 1 1 d . . .
C16 C 0.3795(3) 0.2462(5) 0.6864(2) 0.0461(11) Uani 1 1 d . . .
H16a H 0.4023 0.3415 0.6936 0.069 Uiso 1 1 calc R . .
H16b H 0.4180 0.1791 0.7180 0.069 Uiso 1 1 calc R . .
H16c H 0.3303 0.2442 0.7038 0.069 Uiso 1 1 calc R . .
C17 C 0.3288(3) 0.0797(4) 0.5695(3) 0.0426(10) Uani 1 1 d . . .
H17a H 0.3166 0.0115 0.6045 0.057 Uiso 1 1 calc R . .
H17b H 0.3184 0.0597 0.5145 0.057 Uiso 1 1 calc R . .
O1' O 0.8099(2) 0.5816(4) 0.2514(2) 0.0594(10) Uani 1 1 d . . .
N1' N 0.9240(2) 0.6489(3) 0.52356(19) 0.0363(8) Uani 1 1 d . . .
C1' C 0.9032(2) 0.7187(4) 0.4513(2) 0.0323(9) Uani 1 1 d . . .
C2' C 0.9183(3) 0.8739(4) 0.4381(2) 0.0361(9) Uani 1 1 d . . .
H2a' H 0.9751 0.8876 0.4389 0.048 Uiso 1 1 calc R . .
H2b' H 0.9073 0.9310 0.4815 0.048 Uiso 1 1 calc R . .
C3' C 0.8647(3) 0.9243(5) 0.3580(3) 0.0535(12) Uani 1 1 d . . .
H3a' H 0.8103 0.9408 0.3640 0.071 Uiso 1 1 calc R . .
H3b' H 0.8853 1.0159 0.3444 0.071 Uiso 1 1 calc R . .
C4' C 0.8593(4) 0.8223(5) 0.2896(3) 0.0562(13) Uani 1 1 d . . .
H4a' H 0.9100 0.8270 0.2738 0.075 Uiso 1 1 calc R . .
H4b' H 0.8162 0.8549 0.2438 0.075 Uiso 1 1 calc R . .
C5' C 0.8430(3) 0.6654(5) 0.3064(2) 0.0400(10) Uani 1 1 d . . .
C6' C 0.8677(2) 0.6178(4) 0.3900(2) 0.0352(9) Uani 1 1 d . . .
C7' C 0.8642(2) 0.4801(4) 0.4295(3) 0.0369(9) Uani 1 1 d . . .
C8' C 0.8357(3) 0.3374(5) 0.4147(3) 0.0500(12) Uani 1 1 d . . .
H8' H 0.8111 0.3051 0.3625 0.067 Uiso 1 1 calc R . .
C9' C 0.8460(3) 0.2468(5) 0.4817(4) 0.0532(13) Uani 1 1 d . . .
H9' H 0.8279 0.1523 0.4719 0.071 Uiso 1 1 calc R . .
C10' C 0.8806(3) 0.2848(5) 0.5610(4) 0.0562(14) Uani 1 1 d . . .
H10' H 0.8846 0.2183 0.6026 0.075 Uiso 1 1 calc R . .
C11' C 0.9093(3) 0.4244(5) 0.5777(3) 0.0431(11) Uani 1 1 d . . .
C12' C 0.8996(2) 0.5084(4) 0.5099(3) 0.0361(9) Uani 1 1 d . . .
C13' C 0.9485(3) 0.5236(5) 0.6491(3) 0.0498(12) Uani 1 1 d . . .
H13a' H 1.0030 0.4907 0.6760 0.066 Uiso 1 1 calc R . .
H13b' H 0.9162 0.5248 0.6882 0.066 Uiso 1 1 calc R . .
C14' C 0.9514(2) 0.6783(4) 0.6120(2) 0.0351(9) Uani 1 1 d . . .
H14' H 1.0075 0.7145 0.6264 0.047 Uiso 1 1 calc R . .
C15' C 0.8960(3) 0.7858(5) 0.6368(2) 0.0370(10) Uani 1 1 d . . .
C16' C 0.8085(3) 0.7476(5) 0.6184(3) 0.0451(11) Uani 1 1 d . . .
H16a' H 0.7998 0.6558 0.5916 0.068 Uiso 1 1 calc R . .
H16b' H 0.7769 0.8198 0.5837 0.068 Uiso 1 1 calc R . .
H16c' H 0.7921 0.7426 0.6679 0.068 Uiso 1 1 calc R . .
C17' C 0.9261(3) 0.9074(5) 0.6738(3) 0.0498(12) Uani 1 1 d . . .
H17a' H 0.8917 0.9730 0.6894 0.066 Uiso 1 1 calc R . .
H17b' H 0.9815 0.9270 0.6842 0.066 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 107.8(3) . . ?
C1 N1 C14 140.9(3) . . ?
C12 N1 C14 109.9(3) . . ?
N1 C1 C6 108.3(3) . . ?
N1 C1 C2 125.7(3) . . ?
C6 C1 C2 126.0(3) . . ?
C1 C2 C3 109.1(3) . . ?
C4 C3 C2 111.5(3) . . ?
C3 C4 C5 115.0(4) . . ?
O1 C5 C6 122.1(4) . . ?
O1 C5 C4 122.8(4) . . ?
C6 C5 C4 115.1(3) . . ?
C1 C6 C7 108.0(3) . . ?
C1 C6 C5 120.0(4) . . ?
C7 C6 C5 132.0(4) . . ?
C12 C7 C8 112.8(4) . . ?
C12 C7 C6 103.9(3) . . ?
C8 C7 C6 143.2(4) . . ?
C9 C8 C7 117.9(4) . . ?
C8 C9 C10 125.5(4) . . ?
C11 C10 C9 117.0(4) . . ?
C12 C11 C10 114.5(4) . . ?
C12 C11 C13 106.3(3) . . ?
C10 C11 C13 139.2(4) . . ?
C11 C12 N1 115.5(4) . . ?
C11 C12 C7 132.3(4) . . ?
N1 C12 C7 111.9(3) . . ?
C11 C13 C14 105.2(3) . . ?
N1 C14 C15 110.4(3) . . ?
N1 C14 C13 102.3(3) . . ?
C15 C14 C13 114.0(3) . . ?
C17 C15 C16 123.4(4) . . ?
C17 C15 C14 120.4(4) . . ?
C16 C15 C14 116.2(3) . . ?
C1' N1' C12' 107.7(3) . . ?
C1' N1' C14' 140.9(3) . . ?
C12' N1' C14' 110.4(3) . . ?
N1' C1' C6' 108.5(4) . . ?
N1' C1' C2' 125.8(3) . . ?
C6' C1' C2' 125.6(3) . . ?
C1' C2' C3' 110.5(3) . . ?
C4' C3' C2' 114.5(4) . . ?
C3' C4' C5' 115.9(4) . . ?
O1' C5' C6' 121.0(4) . . ?
O1' C5' C4' 121.8(4) . . ?
C6' C5' C4' 117.2(3) . . ?
C1' C6' C5' 119.1(4) . . ?
C1' C6' C7' 107.4(3) . . ?
C5' C6' C7' 133.6(4) . . ?
C12' C7' C8' 113.5(4) . . ?
C12' C7' C6' 103.7(3) . . ?
C8' C7' C6' 142.7(4) . . ?
C9' C8' C7' 117.1(5) . . ?
C10' C9' C8' 125.8(5) . . ?
C9' C10' C11' 118.6(5) . . ?
C12' C11' C10' 113.5(5) . . ?
C12' C11' C13' 105.2(4) . . ?
C10' C11' C13' 141.2(4) . . ?
N1' C12' C11' 115.6(4) . . ?
N1' C12' C7' 112.7(4) . . ?
C11' C12' C7' 131.5(4) . . ?
C11' C13' C14' 106.2(3) . . ?
N1' C14' C15' 110.8(3) . . ?
N1' C14' C13' 102.0(3) . . ?
C15' C14' C13' 113.7(3) . . ?
C17' C15' C16' 122.9(4) . . ?
C17' C15' C14' 120.3(4) . . ?
C16' C15' C14' 116.7(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.228(5) . ?
N1 C1 1.367(5) . ?
N1 C12 1.377(5) . ?
N1 C14 1.482(5) . ?
C1 C6 1.413(5) . ?
C1 C2 1.470(5) . ?
C2 C3 1.527(5) . ?
C3 C4 1.510(6) . ?
C4 C5 1.522(6) . ?
C5 C6 1.458(6) . ?
C6 C7 1.446(6) . ?
C7 C12 1.389(6) . ?
C7 C8 1.412(6) . ?
C8 C9 1.385(7) . ?
C9 C10 1.427(8) . ?
C10 C11 1.389(6) . ?
C11 C12 1.355(6) . ?
C11 C13 1.528(6) . ?
C13 C14 1.583(5) . ?
C14 C15 1.510(5) . ?
C15 C17 1.323(6) . ?
C15 C16 1.507(6) . ?
O1' C5' 1.235(5) . ?
N1' C1' 1.356(5) . ?
N1' C12' 1.370(5) . ?
N1' C14' 1.486(5) . ?
C1' C6' 1.417(6) . ?
C1' C2' 1.490(6) . ?
C2' C3' 1.506(6) . ?
C3' C4' 1.488(7) . ?
C4' C5' 1.523(7) . ?
C5' C6' 1.449(6) . ?
C6' C7' 1.453(6) . ?
C7' C12' 1.373(6) . ?
C7' C8' 1.410(6) . ?
C8' C9' 1.395(8) . ?
C9' C10' 1.374(8) . ?
C10' C11' 1.387(7) . ?
C11' C12' 1.370(6) . ?
C11' C13' 1.534(7) . ?
C13' C14' 1.574(6) . ?
C14' C15' 1.506(5) . ?
C15' C17' 1.329(7) . ?
C15' C16' 1.481(6) . ?
